How skateboard legend Tony Hawk plans for the long road ahead

Hawk is successful off a skateboard, working as an entrepreneur, philanthropist and investor. Reuters

When most people hear the name Tony Hawk, they picture him whirling through a 900 on his skateboard at ESPN’s X-Games, or on the cover of the iconic video game series, Tony Hawk’s Pro Skater, which has collectively sold millions of copies.

But Hawk, 48, is also successful off a skateboard, working as an entrepreneur, philanthropist and investor. Over the past three decades, he has founded Birdhouse Skateboards, the Tony Hawk Foundation and invested in tech companies from DocuSign to Nest.

Hawk recently spoke with Reuters about the financial lessons he has learned over the years, from his days as a high-flying teenage skate champion to a father of teenagers today.

Q: Did you have any jobs before skateboarding professionally?

A: My only real job was a paper route for a while. I turned pro in skating when I was 14. It wasn’t lucrative at the time, but for a 14-year-old, making like $150 at a competition was a pretty big deal. I basically saved all my earnings until I was 16, and I had enough to buy a moped. To me that was functioning as a semi-adult.

Q: When did your career take off?

A: There were bigger sponsors involved in the competitions; the prize money was going up into the thousands. I was 16, and suddenly making six figures a year. And when you’re 16, that seems like it’s never going to end.

Q: How did you handle that much money as a teenager?

A: I was lucky that I had my dad to give me a dose of reality. He said: ‘You really should be putting this money away for the future.’

I wasn’t really looking toward the future. I was just looking at, like, I could buy a cool car, and I could take all my friends to Hawaii, and stuff like that. He just encouraged me to invest, so I actually bought a house in Carlsbad, California, while I was a senior in high school.

Looking back, I was thankful for that because in ‘91, ‘92, everything came to a screeching halt for skating. My income was dropping by half every month. I had this safety net in this house. I ended up moving back to that place.

A: I sensed that my pro skate career was ending. I actually took out a second mortgage on that house, and pooled my funds with another former pro skater. We started a brand based on the idea that skateboarding would come back around. That was a big gamble.

Q: How do you invest your money today?

A: At first my investment strategy was pretty standard - just mutual funds and stocks, things like that. But I’ve started dabbling in startup investing.

I invested in Nest early on (the Internet-enabled thermostat maker was acquired by Google for $3.2 billion in 2014). I’ve invested in Blue Bottle Coffee and a brewery in San Diego called Black Plague. Also DocuSign and a few other tech companies. I like startups because I like being on the ground floor of stuff, when my support matters.

Q: The Tony Hawk Foundation has built over 550 skate parks in low-income areas in the United States. Why skate parks?

A: I saw how prolific skateboarding had become, but most of the facilities were built in affluent areas. And city councils were not including local skaters in the process of design or construction. I remember I got invited to a few of these grand openings of skate parks. They’d hired the lowest-bidding cement contractors, and the design made no sense - there was a set of stairs that ended with a wall. I thought, ‘I can bridge this gap.’

Q: What lessons do you want to pass on to your own children?

A: You can live comfortably and be happy and not always aspire for something bigger and better – for more. I did that for a big part of my life, and realized that it’s more fun to embrace what you have and to enjoy those things, even if it’s not the most expensive or flashiest.